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PRACTICAL ORGANIC CHEMISTRY

I

Properties.—Colourless rhombic plates ; m.p. 151°; scarcely
soluble in water, easily soluble in alcohol or ether.
Phenyl Thiocarbimide (Phenyl Mustard Oil), CGHSN:CS
The thiocarbanilide is boiled with two to three times tlie
weight of concentrated hydrochloric acid in a flask wit la <m
upright condenser for half an hour. It is decomposed into
triphenylguanidincj which remains as the hydrochloride in solu-
tion (it is subsequently separated) and phenyl mustard oil, wliich
separates out as a brown oil. On distilling the product in
steam, the phenyl mustard oil is carried over into the receiver.
It is separated by shaking out with ether, and removing" tlie
ethereal layer with a tap-funnel It is dehydrated over
calcium chloride, and decanted into a small distilling fla.sk.
The ether is removed on the water-bath and the mustard oil
distilled, with the thermometer, using a short condenser tul:>e»
Yield, 9—10 grams.
Properties.—Colourless oil with a peculiar smell; b. p. 220° ;
sp.gr. 1-135 at 15°.
Reactions.—i. Heat gently for a few minutes 0*5 c.c. phenyl
mustard oil, 0*5 c.c. alcohol and \\ c.c. concentrated ammonia-
On cooling, thiocarbanilamide, NH;j.CS.NH.CGH5, crystallises in
needles.
2.  Heat gently 0*5 c.c, phenyl mustard oil, and 0*5 c,c. aniline ;
on   cooling   and rubbing  with   a   glass   rod,   thiocarbanilide
crystallises.
3.  Heat on the water-bath in a small flask with upright con-
denser 3 grams of phenyl mustard oil and 10 c.c. absolute alcoliol
for 3  hours,  and  pour  into cold  water.    Phenylthiouretlioiio,
. C(jM5NH.CS.OC2H5,  separates out  and may be recrystallisccl
-from alcohol.    Yield, 2|- grams ; m. p. 67°.
4.  Heat a few drops of the mustard oil with yellow mercuric
oxide and notice the irritating smell of phenyl carbimicle.
CGH5N :CS + HgO = C0H5N :CO + HgS
Triphenylguanidina—In order to separate the tripheiiyl-
guanidine remaining in the flask as hydrochloride after distilling-
off the phenyl mustard oil, the hot solution must be somewhat
concentrated. The colourless salt, which crystallises out on. cool-